RTI-121

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IUPAC_name = propan-2-yl (1R,2S,3S)-3-(4-iodophenyl) -8-methyl-8-azabicyclo [3.2.1] octane-2-carboxylate


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CAS_number = 146145-21-3
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PubChem = 122190
C=18 | H=24 | I=1 | N=1 | O=2
molecular_weight = 413.29 g/mol
smiles = CC(C)OC(=O) [C@@H] 1 [C@H] 2CCC(N2C)C [C@@H] 1C3=CC=C(C=C3)I
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legal_status = Legal
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(-)-2β-Carboisopropoxy-3β-(4-iodophenyl)tropane (RTI-121, IPCIT) is a stimulant drug used in scientific research, which was developed in the early 1990s. [Scheffel U, Dannals RF, Wong DF, Yokoi F, Carroll FI, Kuhar MJ. Dopamine transporter imaging with novel, selective cocaine analogs. "Neuroreport". 1992 Nov;3(11):969-72.] RTI-121 is a phenyltropane based, highly selective dopamine reuptake inhibitor [Boja JW, Cadet JL, Kopajtic TA, Lever J, Seltzman HH, Wyrick CD, Lewin AH, Abraham P, Carroll FI. Selective labeling of the dopamine transporter by the high affinity ligand 3 beta-(4- [125I] iodophenyl)tropane-2 beta-carboxylic acid isopropyl ester. "Molecular Pharmacology". 1995 Apr;47(4):779-86.] and is derived from methylecgonidine. RTI-121 is a potent and long-lasting stimulant, producing stimulant effects for more than 10 hours after a single dose in mice [Fleckenstein AE, Kopajtic TA, Boja JW, Carroll FI, Kuhar MJ. Highly potent cocaine analogs cause long-lasting increases in locomotor activity. "European Journal of Pharmacology". 1996 Sep 12;311(2-3):109-14.] which would limit its potential uses in humans, as it might have significant abuse potential if used outside of a strictly controlled medical setting. However RTI-121 occupies the dopamine transporter more slowly than cocaine, and so might have lower abuse potential than cocaine itself. [Stathis M, Scheffel U, Lever SZ, Boja JW, Carroll FI, Kuhar MJ. Rate of binding of various inhibitors at the dopamine transporter in vivo. "Psychopharmacology (Berlin)". 1995 Jun;119(4):376-84.]

Uses

RTI-121 is mainly used in scientific research into the dopamine reuptake transporter. It is more selective for the dopamine transporter than other DAT radioligands such as β-CIT, and so has less nonspecific binding and produces "cleaner" images. [Scanley BE, al-Tikriti MS, Gandelman MS, Laruelle M, Zea-Ponce Y, Baldwin RM, Zoghbi SS, Hoffer PB, Charney DS, Wang S, et al. Comparison of [123I] beta-CIT and [123I] IPCIT as single-photon emission tomography radiotracers for the dopamine transporter in nonhuman primates. "European Journal of Nuclear Medicine". 1995 Jan;22(1):4-11.] [Scanley BE, Gandelman MS, Laruelle M, Al-Tikriti MS, Baldwin RM, Zoghbi SS, Hoffer PB, Wang S, Neumeyer JL, Innis RB. [123I] IPCIT and [123I] beta-CIT as SPECT tracers for the dopamine transporter: a comparative analysis in nonhuman primates. "Nuclear Medicine and Biology". 2000 Jan;27(1):13-21.] Various radiolabelled forms of RTI-121 (with different radioactive isotopes of iodine used depending on the application) are used in both humans and animals to map the distribution of dopamine transporters in the brain. [Chen NH, Ding JH, Wang YL. Characterization of [125I] RTI-121 binding to dopamine transporter in vitro. "Zhongguo Yao Li Xue Bao". 1997 Mar;18(2):115-20. ] [Lever JR, Scheffel U, Stathis M, Seltzman HH, Wyrick CD, Abraham P, Parham K, Thomas BF, Boja JW, Kuhar MJ, Carroll FI. Synthesis and in vivo studies of a selective ligand for the dopamine transporter: 3 beta-(4- [125I] iodophenyl) tropan-2 beta-carboxylic acid isopropyl ester ( [125I] RTI-121). "Nuclear Medicine and Biology". 1996 Apr;23(3):277-84.]

Legal Status

RTI-121 is legal in all countries throughout the world as of 2007. Some jurisdictions such as the USA, Canada, Australia and New Zealand might however consider RTI-121 to be a controlled substance analogue of cocaine on the grounds of its related chemical structure.

References

External links